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Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides

Rehnberg, Nicola LU orcid and Magnusson, Göran LU (1990) In Journal of Organic Chemistry 55(20). p.5467-5476
Abstract

The chiral aldehydes (-)-(2S,5S)- and (-)-(2S,5R)-2-[[[dimethyl( 1,1,2-trimethylpropyl)silyl]oxy]methyl]-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15% yield, respectively, by lithium bromide induced rearrangement of 6-O-silylated methyl 2,3- and 3,4-anhydro-a- and -d-D-hexopyranosides, obtained in two steps from methyl α- and β-D-glucopyranoside. Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes. Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.

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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
55
issue
20
pages
10 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:0001263595
ISSN
0022-3263
DOI
10.1021/jo00307a017
language
English
LU publication?
yes
id
d0d052f2-a53e-41e4-b2be-5aca5ac79638
date added to LUP
2021-11-11 11:54:22
date last changed
2021-11-16 02:28:15
@article{d0d052f2-a53e-41e4-b2be-5aca5ac79638,
  abstract     = {{<p>The chiral aldehydes (-)-(2<i>S</i>,5<i>S</i>)- and (-)-(2<i>S</i>,5<i>R</i>)-2-[[[dimethyl( 1,1,2-trimethylpropyl)silyl]oxy]methyl]-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15% yield, respectively, by lithium bromide induced rearrangement of 6-<i>O</i>-silylated methyl 2,3- and 3,4-anhydro-a- and -d-D-hexopyranosides, obtained in two steps from methyl <i>α</i>- and <i>β</i>-D-glucopyranoside. Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes. Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.</p>}},
  author       = {{Rehnberg, Nicola and Magnusson, Göran}},
  issn         = {{0022-3263}},
  language     = {{eng}},
  number       = {{20}},
  pages        = {{5467--5476}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Organic Chemistry}},
  title        = {{Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides}},
  url          = {{http://dx.doi.org/10.1021/jo00307a017}},
  doi          = {{10.1021/jo00307a017}},
  volume       = {{55}},
  year         = {{1990}},
}